28447-16-7

Usage

Uses

Used in Pharmaceutical Synthesis:
4-(Pyridin-3-yl)-but-3-en-2-one is used as a key intermediate in the synthesis of pharmaceuticals for its ability to participate in various chemical reactions such as nucleophilic addition and substitution. Its structural versatility and reactivity contribute to the development of new medicinal compounds.
Used in Agrochemical Production:
In the agrochemical industry, 4-(Pyridin-3-yl)-but-3-en-2-one serves as a valuable building block in the creation of agrochemicals, leveraging its chemical properties to enhance the effectiveness of these products.
Used in Fine Chemicals Synthesis:
4-(Pyridin-3-yl)-but-3-en-2-one is also utilized in the synthesis of other fine chemicals, where its unique structure and reactivity are harnessed to produce specialty chemicals for various applications.
Used in Medicinal Chemistry and Drug Design:
4-(Pyridin-3-yl)-but-3-en-2-one is employed as a structural component in medicinal chemistry and drug design, capitalizing on its potential biological activity and diverse synthetic applications to create innovative pharmaceutical agents.
Overall, the applications of 4-(Pyridin-3-yl)-but-3-en-2-one span across multiple industries, highlighting its importance as a versatile building block in the synthesis of complex organic molecules.

Upstream product

• 500-22-1 3-pyridinecarboxaldehyde 
• 67-64-1 acetone 
• 54756-29-5 2-acetyl-3ξ-[3]pyridyl-acrylic acid ethyl ester 
• 105900-69-4 2-(hydroxy-[3]pyridyl-methyl)-acetoacetic acid ethyl ester 
• 2091-46-5 triphenyl(prop-2-ynyl)phosphonium bromide 
• 123-75-1 pyrrolidine 
• 78-95-5 chloroacetone 
• 626-55-1 3-Bromopyridine 
• 78-94-4 methyl vinyl ketone 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 

Downstream Products

• 300805-77-0 C₉H₁₁NO 

Relevant academic research and scientific papers

Rate dependence on inductive and resonance effects for the organocatalyzed enantioselective conjugate addition of alkenyl and alkynyl boronic acids to β-indolyl enones and β-pyrrolyl enones

Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone β-position. For the former, the closer the heteroatom is to the enone β-carbon, the faster the reaction. For the latter, greater resonance stabilization of the benzylic cationic charge accelerates the reaction. Thus, reaction rates are increased by the closer proximity of inductive electron-withdrawing elements, but if resonance effects are involved, then increased rates are observed with electron-donating ability. Evidence for these trends in isomeric substrates is presented, and the application of these insights has allowed for reaction conditions that provide improved reactivity with previously problematic substrates.

Balanced dual acting compounds targeting aromatase and estrogen receptor α as an emerging therapeutic opportunity to counteract estrogen responsive breast cancer

Breast Cancer (BC) is a leading cause of death in women, currently affecting 13% of female population worldwide. First-line clinical treatments against Estrogen Receptor positive (ER+) BC rely on suppressing estrogen production, by inhibiting the aromatase (AR) enzyme, or on blocking estrogen-dependent pro-oncogenic signaling, by targeting Estrogen Receptor (ER) α with selective Modulators/Degraders (SERMs/SERDs). The development of dual acting molecules targeting AR and ERα represents a tantalizing alternative strategy to fight ER + BC, reducing the incidence of adverse effects and resistance onset that limit the effectiveness of these gold-standard therapies. Here, in silico design, synthesis, biological evaluation and an atomic-level characterization of the binding and inhibition mechanism of twelve structurally related drug-candidates enable the discovery of multiple compounds active on both AR and ERα in the sub-μM range. The best drug-candidate 3a displayed a balanced low-nanomolar IC50 towards the two targets, SERM activity and moderate selectivity towards a BC cell line. Moreover, most of the studied compounds reduced ERα levels, suggesting a potential SERD activity. This study dissects the key structural traits needed to obtain optimal dual acting drug-candidates, showing that multitarget compounds may be a viable therapeutic option to counteract ER + BC.

One-pot two-step chemoenzymatic deracemization of allylic alcohols using laccases and alcohol dehydrogenases

A series of enantioenriched (hetero)aromatic secondary allylic alcohols has been synthesized through deracemization of the corresponding racemic mixtures combining a non-selective chemoenzymatic oxidation (laccase from Trametes versicolor and oxy-radical TEMPO) and a stereoselective biocatalyzed reduction (lyophilized cells of E. coli overexpressing an alcohol dehydrogenase, ADH). Both steps were performed in aqueous medium under very mild reaction conditions. After optimization, a sequential one-pot two-step protocol was set up, obtaining the corresponding chiral alcohols in moderate to high conversions (48–95%) and enantiomeric excess (65->99% ee). Depending on the ADH stereopreference, both antipodes from these valuable chiral synthons could be prepared, even at preparative scale (119?178 mg), in a straightforward manner.

Sequential Two-Step Stereoselective Amination of Allylic Alcohols through the Combination of Laccases and Amine Transaminases

A sequential two-step chemoenzymatic methodology for the stereoselective synthesis of (3E)-4-(het)arylbut-3-en-2-amines in a highly selective manner and under mild reaction conditions is described. The approach consists of oxidation of the corresponding racemic alcohol precursors by the use of a catalytic system made up of the laccase from Trametes versicolor and the oxy-radical TEMPO, followed by the asymmetric reductive bio-transamination of the corresponding ketone intermediates. Optimisation of the oxidation reaction, exhaustive amine transaminase screening for the bio-transaminations and the compatibility of the two enzymatic reactions were studied in depth in search of a design of a compatible sequential cascade. This synthetic strategy was successful and the combinations of enzymes displayed a broad substrate scope, with 16 chiral amines being obtained in moderate to good isolated yields (29–75 %) and with excellent enantiomeric excess values (94 to >99 %). Interestingly, both amine enantiomers can be achieved, depending on the selectivity of the amine transaminase employed in the system.

Polyethyleneimine-Supported Triphenylphosphine and Its Use as a Highly Loaded Bifunctional Polymeric Reagent in Chromatography-Free One-Pot Wittig Reactions

A polyethyleneimine-supported triphenylphosphine reagent has been synthesized and used as a highly loaded bifunctional homogeneous reagent in a range of one-pot Wittig reactions that afforded high yields of the desired products after simple purification procedures. The approach also served efficiently in tandem reaction sequences involving a one-pot Wittig reaction followed by conjugate reduction of the newly formed alkene product in situ. In these transformations, the phosphine oxide groups generated in the Wittig reaction served as the catalyst for activating trichlorosilane in the subsequent reduction reaction.

A general method for the enantioselective synthesis of α-chiral heterocycles

The enantioselective formation of stereocenters proximal to unprotected heterocycles has been accomplished. Thus, vinyl boronic acids are added to heterocycle-appended enones via a modified-BINOL catalyst. Catalyst design was key to enable a general reaction. High yields and useful er's are observed for a host of common heteroaryls.

Preparation of monometallic (Pd, Ag) and bimetallic (Pd/Ag, Pd/Ni, Pd/Cu) nanoparticles via reversed micelles and their use in the Heck reaction

The metal nanoparticles (NPs) have been prepared using a water-in-oil microemulsion system of water/dioctyl sulfosuccinate sodium salt (aerosol-OT, AOT)/isooctane at 25 °C. Since the NPs produced in this system can endure forcing conditions (100 °C), this system has been used for the synthesis of nano-catalysts in the Heck reactions. FE-SEM, DLS, and UV/vis analyses have been used to characterize the surface morphology, size, and proof of the formation of all the prepared metal NPs, respectively. In addition, the effects of some reaction parameters (here, bases and solvents) were optimized. Differences in the catalytic properties of the synthesized NPs have also been investigated. Consequently, the Pd/Cu (4:1) bimetallic NP showed the highest activity in the C-C coupling reaction of the iodobenzene with the styrene, thus it is employed as the superior catalyst in this study. Therefore, the Pd/Cu (4:1) bimetallic NPs were further investigated using TEM and XRD analyses. This catalyst system is also reusable for six runs with very negligible reduction in the efficiency.

Morpholinium trifluoroacetate-catalyzed aldol condensation of acetone with both aromatic and aliphatic aldehydes

We report a highly efficient, general and practical method for the aldol condensation of acetone with aromatic and aliphatic aldehydes, using morpholinium trifluoroacetate as a catalyst.

A convenient route to (E)-α,β-unsaturated methyl ketones

Aldehydes are converted into (E)-α,β-unsaturated methyl ketones in good yield and with a high E stereoselectivity using α,α- bis(trimethylsilyl) N-tert-butyl acetimine 3. The reaction was mediated by a catalytic amount of tetrabutylammonium fluoride (TBAF) under mild conditions. The disilylated reagent 3 is easily generated from N-tert-butylacetimine, lithium diisopropylamide (LDA), and chlorotrimethylsilane. The mechanism of the reaction is discussed. Copyright

Solid phase synthesis of 2-aminobutadienes using a piperazine linker

A series of resin-bound 4-substituted-2-aminobutadienes have been synthesised via Wittig reaction with polymer supported 2-(N-piperazino)prop-1-enyl-1-triphenylphosphonium bromide. The use of piperazine provides a readily cleavable enamine linker for attachment of ketones that is compatible with anion chemistry.